Functional Groups, A Short List
Oxygen-containing Diketene
Acetal/ketal
Acid anhydride Ester
Acyl halide Ether
X = Cl, Br, I Ethylenedioxy- (crown ether)
Acylal
Hemiacetal/Hemiketal Alcohol
Homoallylic Carbonate
Hydroperoxide
Carboxylic acid/carboxylate anion
Ketene
Chloroformate ester
Ketone/aldehyde
Dicarbonate
Lactone
1
Methylenedioxy- Amide
Orthocarbonate ester Amidine
Orthoester
Amidrazone
Peroxide
Amine Ynol*
*Highly unstable, tautomer of ketene Azide
Ynone Azine
Nitrogen-containing Azo group
Acylurea
Azoxy
Aldimine (primary/secondary)
Carbamate
2
Carbazide Hydroxamic acid
Carbodiimide Imide
Carboximidate Imidic acid
Cyanate Isocyanate
Cyanimide Isonitrile
Diazo group Ketenimine
Enamide Ketimine (primary/secondary)
Enamine Lactam
Hydrazone
Nitrile (cyanide)
Nitrite
3
Nitrosamine Dithiocarboxylic acid ester
Nitroso Isothiocyanate
Oxime S-nitrosothiol
Sulfate Semicarbazide
Sulfenamide Semicarbazone
Sulfenyl chloride
Triazene
Sulfinic acid
Sulfur-containing Sulfite
Disulfide
Sulfonate ester Dithiocarbamate
Sulfone Dithiocarboxylic acid
4
Sulfonic acid Thioketene
Sulfonyl Thiol
X = Cl, Br, I Thiolester
Sulfoxide
Thionoester
Sulfuryl
Thiosemicarbazide
X = Cl, Br, I
Thial
Thiourea
Thiocarboxylic acid (O)
Phosphorus-containing Thiocarboxylic acid (S) Phosphate
Thiocyanate
Phosphine
Thioether (sulfide)
Phosphodiester Thioketone
5
Phosphonate Siloxy group
Silyl chloride Phosphonic acid
Silyl ether Phosphonite
Silyl hydride Phosphoramide
Phosphoramidite Alkyl groups
Adamantyl group
Silicon-containing
Silanol Allyl group
Benzyl group (–Bn)
Silene
Butyl group
Silole
6
Isobutyl group Boron-containing
Borinic acid t-Butyl group
Borinic ester
Crotyl group (cis/trans)
Boronic acid
Ethyl group
Boronic ester Isoprene
Propyl group Miscellaneous
Acetoxy (–OAc) Isopropyl group
Acetyl group (–Ac) Neopentyl group
Phenyl group (–Ph) Acryloyl group
Propargyl group Acyl group
Vinyl group
7
Benzoyl group (–Bz) Telluroketone*
Tellurol* Enediyne
*Tellurium-containing functional groups are highly unstable
Tosyl group (–Ts)
Nonaflate group
Tosylate (–OTs) Selenenic acid
Seleninic acid
Triflate group (–Tf)
Selenol
Vanillyl group Selenonic acid
Selone Functional groups featuring tautomerism Tautomerization of some of the functional groups found in the notes Tellurocyanate* Keto-enol tautomerization
Telluroester*
8
Imine-enamine tautomerization Azetidine
Oxetane Amide-imidic acid tautomerization
Lactam-lactim tautomerization Oxolane / Tetrahydrofuran
Pyrrolidine / Azolidine Nitroso-oxime tautomerization
Tetrahydrothiophene Ketene-ynol tautomerization
Oxole / Furan
Heterocycles
Epoxide (oxirane) Azole / Pyrrole
Aziridine Thiophene
Episulfide / Thiirane Imidazole
Dioxirane Pyrazole
9
Pyridine Isoxazole
Pyrimidine Oxazole
Pyridazine Thiazole
Pyrazine Triazole (1,2,3 and 1,2,4)
Pyran Tetrahydropyran
4H-Pyran Piperidine / azinane
Tetrahydrothiopyran
Morpholine
Dioxane
10